HCID 23150774, compound → HCID 11978505, compound

HRID 908899Notes

Reaction equation

HRID 908899 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:11][C:10]=1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 23150774HCID 23150774, compound

Product 1

HCID 11978505HCID 11978505, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A A suspension of 10% palladium on charcoal (25 mg) in a solution of trans-1-{3-[3-(4-benzyloxy-3-methoxyphenyl)allyloxy]propyl}piperidine (340 mg containing 28% wt dimethylsufoxide) in methanol (2.5 mL) is stirred overnight at room temperature under an atmosphere of dihydrogene. The suspension is filtered over a clarcel pad and the filtrate concentrated under reduced pressure. The product is dissolved in diethyl oxide and a solution of oxalic acid (61 mg) in acetone is added. The precipitate is filtered, washed with diethyl oxide and dried under vacuum to afford 150 mg of 1-{3-[3-(4-hydroxy-3-methoxyphenyl)propoxy]propyl}-piperidine, oxalate as a white solid melting at 110-111° C.

Workup

  1. filtrationThe suspension is filtered over a clarcel pad
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionThe product is dissolved in diethyl oxide
  4. additiona solution of oxalic acid (61 mg) in acetone is added
  5. filtrationThe precipitate is filtered
  6. washwashed with diethyl oxide
  7. customdried under vacuum

Sources & evidence

ORD record
ord-51158511d08e4f389cd22f53004d30a1
Source dataset
uspto-grants-2011_09
Patent number
US08017646B2

Reaction notes

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